J. Bio. Env. Sci. 2016 Journal of Biodiversity and Environmental Sciences (JBES) ISSN: 2220-6663 (Print) 2222-3045 (Online) Vol. 8, No. 2, p. 240-248, 2016 http://www.innspub.net RESEARCH PAPER
OPEN ACCESS
Essential oil variation within and between Stachys inflata Benth. and Stachys lavandulifolia Vahl. populations from Iran Seyed Mehdi Shahgolzari*, Afagh Yavari Department of Biology, Payame Noor University, Tehran, Iran Article published on February 28, 2016 Key words: Essential oils, GC–MS, Stachys inflata, Stachys lavandulifolia.
Abstract Although several species of Stachys possess characteristic essential oils, only a few published studies have described within and between populations of their volatile constituents. The aim of the present study was to evaluate the chemical composition of essential oils from two chemically unexplored Stachys species, Stachys lavandulifolia and Stachys inflata. Populations of these species were collected from Touyserkan, Hamedan province west of Iran. The essential oils of the dried flowering aerial parts of two species were isolated by hydrodistillation and analysed by means of GC and GC–MS. In this survey, 12 populations of both species were studied. Then data obtained were analyzed by Pc-ord software. 64 oil components were identified. 6, 10, 14trimethyl-2-pentadecanone, Dibutylphthalate, isobutyl phthalate, spathulenol, trans-caryophyllene and αcopaene was observed in all populations of two species. δ-3-carene, Mytenal and α-thujene only in S. lavandulifolia and E-Citral (Geranial), n-docosane, neryl acetate, Nerylphenylacetate, Z-citral (Neral) only in S. inflata was observed. No similarity was observed between the chemical profile of essential oils obtained from S. lavandulifolia and S. inflata. The results of the present study indicated that essential oil components of S. lavandulifolia and S. inflata could be varied within and between populations. *Corresponding
Author: Seyed Mehdi Shahgolzari Mehdi.shahgolzari@gmail.com
240 | Shahgolzari and Yavari
J. Bio. Env. Sci. 2016 Introduction
were collected in different habitats from Touyserkan,
The genus Stachys, one of the largest genera of the
Hamedan province west of Iran (May 2013).
Labiatae (Lamiaceae) family with around 300 taxa, is widely distributed across the world from tropical to
Plant material and essential oil preparation
subtropical regions (Piozzi and Bruno, 2009 &, 2011).
The
The genus is geographically wide spread and found
lavandulifolia and S. inflata were collected at full
mostly in the Mediterranean, South Western Asia,
flowering stage. A voucher specimen (code numbers
North and South America and South Africa. The
of
native species are, however, absent in New Zealand
deposited at the Herbarium of Biology Department,
and
Stachys
Payame Noor University, Touyserkan, Hamedan,
lavandulifolia Vahl. and Stachys inflata Benth. type
Iran. The air-dried materials were finely ground, then
of Stachys genus (Lamiaceae family) has been widely
subjected to hydro-distillation for 3 hours with water
studied based on its essential oil and therapeutic
as solvent, using a Clevenger apparatus according to
characteristics over the recent decades. In Previous
the standard procedures. The oils were stored at 4 oC
studies
for further analyses.
Australia
on
S.
(Bhattacharjee,
lavandulifolia
1980).
(Ghannadi
and
aerial
parts
populations
of
different
1001-1012)
of
populations
population
S.
was
Alemdoost, 1996; Alamdoost, 1996; Feizbaksh et al., 2003; Javidnia et al., 2004; Hajhashemi et al., 2006;
Gas chromatography–mass spectrometry (GC–MS)
Meshkatalsadat et al., 2007; Amiri et al., 2009; Asadi
Volatile components were identified by GC-MS using
et al., 2010; Nadaf et al., 2011; Sadrmomtaz et al.,
a Finnigan TRACE GC-MS (Thermo Quest Finnigan
2011; Pirbalouti et al., 2011; Jafarzadeh et al., 2012;
Co., USA) equipped with a DB-1 capillary column (60
Soleimani- Meimand et al., 2013; Aghaei et al., 2013;
m × 0.25 mm × 25µm). Helium (flow rate, 1.1
Pirbalouti and Mohammadi, 2013; Meimand et al.,
ml/min) was used as the carrier gas, and injection
2013; Tundis et al., 2015) and S. inflata (Garjani et
volumes were 0.2 µl. The oven temperature was
al., 2004; Sajjadi and Somae, 2004; Norouzi-Arasi et
raised from 60 ºC to 250 ºC at a rate of 5 ºC /min,
al., 2005; Ebrahimabadi et al., 2009; Nabizahedasl et
held at 250 ºC for 5 min; transfer line temperature
al., 2010; Rustaiyan et al., 2011; Omidbaigi et al.,
was 250 ºC. Split ratio was 100. The quadruple mass
2013; Yavari and Shahgolzari, 2013; Shahbazi et al.,
spectrometer was scanned over the 40-460 amu with
2014; Talebi et al., 2014) different compounds of oil
an ionizing voltage of 70 eV and the injector
were reported. The differences in qualitative and
temperatures were kept at 250 ºC. The constituents of
quantitative compositions of the essential oils were
the oil were identified by calculation of their retention
found on both specific and population levels.
indices under programmed temperature conditions
According to existing references and information,
for n-alkanes (C8-C24) and the oil on a DB-1 column
individuals of this species are present in many
under
stations with different ecological conditions. We are
individual compounds was made by comparison of
becoming increasingly aware that an individual
their mass spectra with those of the internal reference
cannot be considered out of the context of its
mass spectra library or with authentic compounds
environment. With regard to the wide distribution of
and confirmed by comparison of their retention
S. lavandulifolia and S. inflata in Iran we wanted to
indices with authentic compounds or with those
know if there is essential oil diversity within and
reported in the literature (Adams, 2001).
the
same
conditions.
Identification
of
between populations of these species in studied area. Chemical variability Material and methods
Analytical data for cluster analysis were treated by
Location
means of the Pcord-4 with group linkage method
12 populations of wild S. lavandulifolia and S. inflata
(nearest neighbor).
241 | Shahgolzari and Yavari
J. Bio. Env. Sci. 2016 Results and discussion
moderate antibacterial activity of ß-caryophyllene and
The essential oil compositions of the Stachys genus
germacrene D were reported. Germacrenes were
have been well documented in the literature, but not
produced as antimicrobial and insecticidal agents
for all the species have been described in detail. The
from Stachys species (Omura et al., 2006; Goren et
main components of the essential oil of the species
al., 2011). α- pinene, ß-caryophyllene, linalool oxide
were observed to be germacrene D, caryophyllenes,
and caryophyllene oxide were tested against several
cadinene,
bacterial strains.
spathuleneol
and
caryophyllene.
The
Table 1. Essential oil composition of S. lavandulifolia and S. inflata populations from studied area (%). Compounds
1,8-Cineol 4a-α,7-α,7a-α-Nepetalactone 4-Terpineol 6,10,14-trimethyl-2pentadecanone 6,9-Guaiadiene ar-Curcumine bicyclo Elemene bicyclogermacrene Caryophyllene oxide Cembrene cis-sabinene hydrate cis-sesquisabinene hydrate cis-ß-bisabolene cryptone cumin aldehyde δ-3-carene Dibutylphthalate E-Citral( Geranial) E-Nerolidol E-ß-Farnesene E-ß-Ionone Germacrene D humulene epoxide Intermedeol isobutyl phthalate isospathulenol limonene linalool Mytenal n-docosane neryl acetate Nerylphenylacetate n-tetradecane P-Cymene pirollene pristane sabinene Sesquisabinene spathulenol terpinolene trans- verbenol trans-caryophyllene trans-pinocarveol trans-α-bergamotene Viridiflorol Z-citral (Neral) α-bisabolol α-Cadinol α-campholenal
IR 1038 1365 1186 1848
Populations of S.lavandulifolia Khangormaz Serkan P1 P2 P3 P4 1.47 1.57 0.23 0.62 0 0.06 0.07 0.09 0.12 0.03 0 0.05 1.05 0.26 2 1.87
Sarabi P5 0.45 0.03 0 0.47
1454 1492 1350 1517 1608 1964 1072 1565 1551 1194 1248 1017 1969 1272 1569 1460 1496 1501 1633 1684 1874 1658 1035 1100 1205 2204 1381 2013 1401 1029 1103 1709 978 1466 1600 1049 1154 1441 1150 1447 1617 1244 1696 1674
0 0 0 0 16.4 0 0.09 0 0 0.04 0.32 0 4.72 0 0 0 0 0.22 0.13 1.63 18.4 0 0 0.77 0.16 0 0 0 0 0 0 0.63 0 1.78 0.94 0 0.62 14.4 0 0.3 0 0 0 0
1132 0.39
P6 0.4 0 0 1.4
Population of S.inflata Khangormaz Serkan Average P7 P8 P9 P10 0.79 0 0 0 0.2 0.04 0 0.06 0 0.2 0.04 0 0 0 0 1.17 0.54 1.34 5 1.3
Sarabi P11 0.2 0.1 0 0.9
P12 5 0 0.6 0.3
Average 0.9 0.07 0.11 1.6
0.06 0.03 0.43 13.17 3.3 0.25 0.51 0.04 0.27 0 0.27 0.63 1.45 0 0.42 2.3 0.16 8.21 0.22 0.08 3.24 0.87 14.31 0.09 0.18 0 0 0 0.28 0.1 0.1 0.22 0.86 0 10.28 0.93 0.64 14.58 0.16 0.47 0.3 0 0.03 0.17
0.04 0.13 0.02 0.4 16.3 0.18 0.01 0.14 0 0 0.11 0 1.02 0 1.44 1.56 0.53 0.13 0.7 1.17 4.12 2.8 0.13 0.12 0.04 0 0 0 0.17 0 0.04 1.16 0 0 50.7 0.09 0.12 7.98 0.31 0.42 0.68 0 0.07 1
0.13 0.02 0.38 1.96 4.26 0.37 0.05 0.21 0.09 0 0.39 0.07 0.8 0 1.18 4.76 0.2 2.74 0.17 0 0.75 2.01 0.31 0.22 0.21 0 0 0 0.77 0.02 0.22 0.72 0.07 0 40 1.03 2.19 17.7 0.14 1.41 0.41 0 0.02 0.67
0 0.02 0.26 6.84 5.19 0.74 0.02 0.11 0.17 0 0.06 0 4.1 0 0.72 3.67 0.29 4.94 0.15 0 0.72 1.84 2.36 0.06 0.11 0 0 0 0.46 0 0.1 0.99 0.07 0 26.2 0.55 0.55 25 0.25 0.93 0.48 0 0.1 0.24
0.1 0.2 0.1 0.8 0 0.8 0 0.2 0 0.2 0.2 0 2.1 0 0.8 2.2 0.3 0 0 0.7 16 2.4 0.6 0 0 0 0 0 0.8 0.1 0.1 0.6 0 0 52 0.1 0.2 7.8 0.1 0.4 0.9 0 0.1 0
0.06 0.07 0.2 3.87 7.57 0.38 0.12 0.12 0.1 0.03 0.23 0.12 2.36 0 0.75 2.42 0.24 2.71 0.24 0.6 7.22 1.65 2.95 0.22 0.12 0 0 0 0.41 0.03 0.09 0.72 0.17 0.3 30 0.45 0.72 14.6 0.16 0.65 0.47 0 0.05 0.35
0 1.3 0 0 0 0 0 0 0 0 0 0 15.1 3.95 0.18 0 0 0.56 0 0 8.45 0 1.15 0 0 0.25 0.48 6.64 0 0 0 0 0 0.19 41.6 0 0 4.15 0 0 0 2.86 0 1.6
0 0.08 0 0.05 5.84 0.7 0 0 0.05 0 0 0 34.66 0 0.08 0.22 0.08 0.27 0.25 0.91 24.68 0.82 0.24 0 0 0 0 0 0.03 0 0 1.91 0 0 20.15 0.09 0.06 2.15 0 0.07 1.03 0 0.21 0.69
0 0 0 5 18 0 0 0 0 0 0 0 5 0 0 1 2 13 0 4 1 2 0 0 0 0 0 0 1 0 0 1 0 0 21 1 0 7 0 0 3 0 0 0
0.2 0.5 0.2 6.9 4.3 0.4 0 0 0.2 0.2 0.5 0 2.6 0 0 0.3 2.1 6.5 0.7 0 1.1 6 0 0 0 0 0 0 0.3 0 0 1.3 0 0 47 0 0.8 0.9 0 1.1 4.4 0 0 4.5
0.1 0.1 0.6 18 2.6 0.1 0.1 0.1 0.2 0.1 0.2 0.1 5.9 0 0.2 0.9 1 23 0.3 0 0.8 1.7 2.4 0.1 0 0 0 0 0.9 0.1 0 0.7 0.2 0 19 0.1 0.3 3.6 0.2 0.6 1.4 0 0 1
0 6.1 0 0 6.1 0 0.1 0 0 0 0 0 2.5 26 0.7 0 0 0.1 0 0 0.1 0 5.2 0 0 0 0.9 0.2 0 0.6 0.1 0 0.3 0.4 9.5 0 0 4 0 0.1 0 20 0 1.7
0.09 1.34 0.19 4.94 6.18 0.27 0.03 0.02 0.1 0.05 0.16 0 10.9 5.07 0.2 0.33 0.9 7.1 0.22 0.88 5.97 1.72 1.5 0.02 0 0.05 0.23 1.13 0.41 0.13 0.02 0.85 0.08 0.1 26.3 0.17 0.21 3.59 0.05 0.39 1.64 3.78 0.04 1.56
0.43
0.1
0.91
0.46
0.2
0.42
0
0
0
0
0.2
0
0.05
242 | Shahgolzari and Yavari
J. Bio. Env. Sci. 2016 α-copaene α-humulene α-phellandrene α-pinene α-Terpineol α-thujene ß-bourbonene ß-elemene ß-Myrcene ß-phellandrene ß-Pinene γ-Terpinene δ-Cadinene Number of compounds Total oil
1392 1474 1010 940 1197 931 1403 1405 991 1036 985 1063 1538 ----------
0.38 0.38 0 0.29 0.33 0 0 0.05 0 0 0 0.11 0 27 66.1
1.23 0.14 0.28 1.5 0.27 0.17 0.45 0.34 9.39 0 1.06 0.24 2.2 50 99.23
1.14 0.09 0 0 0.16 0 0.16 0.16 0.06 0 0 0 0.21 44 98.2
2.1 0.37 0 0.1 0.68 0.02 0.83 0.44 0.91 2.21 0.14 0.1 1.49 53 99.5
0.76 0.39 0.03 0.07 0.32 0 0.29 0.47 2.49 1.93 0.31 0.07 1.4 49 98.2
2.4 0.2 0 0.1 0.1 0 0.6 0.4 0.1 0.4 0.2 0.1 1.1 42 98
1.34 0.26 0.06 0.35 0.31 0.03 0.38 0.31 2.15 0.75 0.28 0.11 1.07 -------93.3
0.23 0 0 0 0 0 0.07 0 0 0 0 0 0.74 19 90.1
0.07 0 0 0.01 0.11 0 0.02 0.12 0.04 0 0.01 0.04 0.4 29 97.54
2 0 0 0 0 0 2 0 0 0 0 0 2 19 98
1 0.8 0 0 0 0 0.9 0 0 0 0 0 2 31 99
1.4 0.8 0.1 3 0 0 0.1 0.1 0.3 1.4 2.5 0.2 2 49 99
1.1 0 0 0.2 1.2 0 0 0 0 0 0 0 0.5 26 94
The essential oil composition of Stachys species
According to previous studies, various components of
mainly consists of sesquiterpenes and oxygenated
essential oil on this both species have been reported.
sesquiterpenes. Moreover, the monoterpenes such as
This shows that the volatile oil composition of those,
α-pinene, ß-pinene, phellandrene and carvacrol were
in Iran is extremely variable (Naghibi et al., 2005;
also extracted from Stachys species. S. lavandulifolia
Semnani et al., 2006; Arasi et al., 2006; Goudarzi et
and S. inflata are medical plants that can be a
al., 2011).
potential source of monoterpenes and sesquiterpenes.
Fig. 1. Dendrogram representing similarity relationship between S. lavandulifolia and S. inflata species based on essential oil constituents. The essential oil compositions of our samples for S.
based on their essential oil composition (namely
lavandulifolia and S. inflata are shown in Table 1.
analysis of the two species together). 6, 10, 14-
According to the GC mass analysis a total of 62
trimethyl-2-pentadecanone,
compounds were identified in S. lavandulifolia and S.
isobutyl phthalate, spathulenol, trans-caryophyllene
inflata together. The dendrogram (Fig. 1) represents
and α-copaene was observed in all populations of
graphically the relationships between the populations
both species. Based on these results, the essential oil
of S. lavandulifolia and S. inflata and the groups,
variation patterns in Stachys species exhibited more
243 | Shahgolzari and Yavari
Dibutylphthalate,
0.88 0.34 0.01 0.53 0.22 0 0.51 0.04 0.06 0.25 0.43 0.03 1.27 -----96.2
J. Bio. Env. Sci. 2016 diversity. The highest oil compounds in two Stachys
lavandulifolia and E-Citral( Geranial), n-docosane,
species were Spathulenol. The highest percentage was
neryl acetate, Nerylphenylacetate, Z-citral (Neral)
recorded in population 3 (50.7%) and the lowest in
only in S. inflata was observed. No similarity was
population 1 (0.94%). To assess the use of essential
observed between the chemical profile of essential oils
oil constituents in identifying taxonomic relationships
obtained from S. lavandulifolia and S. inflata. Figure
between species, multivariate analysis by nearest
1 shows the separation between populations. On the
neighbor complete linkage cluster analysis were
other hand, the two species from Stachys were
initially performed with oil constituent. Therefore,
clustered in 2 groups, and were clearly different from
two groups of populations were identified. δ-3-
the others.
carene,
Mytenal
and
Îą-thujene
only
in
S.
Fig. 2. Dendrogram representing similarity relationship between S. lavandulifolia populations based on essential oil constituents.
Fig. 3. Dendrogram representing similarity relationship between S. inflata populations based on essential oil constituents.
244 | Shahgolzari and Yavari
J. Bio. Env. Sci. 2016 The dendrogram (Fig. 2, 3) represents graphically the
within and between the species was determined by
relationships within the populations and the groups
using essential oil analysis could prove useful for the
of both species, separately. The major components of
classification of two species in relation with locality of
S. lavandulifolia according to average essential oil in
species. Oil constituents in the Stachys species show
populations
(3.87%),
excessive diversity in Iran and these compounds
(7.57%) isobutyl phthalate
strongly differentiated them. The application of single
(7.22%), spathulenol (30%) and trans-caryophyllene
linkage clustering produced two large clusters within
(14.6%). The highest total essential oil was recorded
the population, it is therefore concluded that essential
in populations 4 (99.5%) and the lowest ratio was
oil
obtained in populations 1 (66.1%).
identification
Caryophyllene
were oxide
bicyclogermacrene
could
be
useful and
markers
classification.
in
population
These
results
suggested that essential oils data could clearly The numbers of identified compounds in the essential
separate different populations of two species from
oil of the 6 populations ranged from 27 to 53. Total
each other. Essential oil analyses of S. lavandulifolia
percentages of identified compounds however, varied
and S. inflata species found in Touyserkan, Hamedan
from 66.1% to 99.5%. The average value of the totally
province west of Iran have revealed high chemical
identified compounds was 93.3% (Table 1). The major
polymorphism in within and between populations,
components of S. inflata according to average
possibly related to edaphic, genetic and ecological
essential oil in populations were Z-citral (Neral)
influences.
(3.78%), bicyclogermacrene (4.94%), Caryophyllene oxide (6.18%) isobutyl phthalate (5.97%), spathulenol
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